Hitting the virtual campaign trail on Monday, President Obama sat down for one-on-one conversations with voters in an online chat hosted by Google Plus. Toward the end of the hour-long session, Christine—an Evanston, IL resident—asked the President about his plans with the First Lady to celebrate their 20th wedding anniversary on Oct. 3.

"Sadly, it's a month before the election," the President told her. "I don't know how romantic a weekend we're actually gonna get. We may have to defer the full celebration until later in November." No romantic plans?! That simply won't do, Mr. President.

Why not return to the scene of your wedding (and squeeze in some quality hometown time) by spending the weekend in Chicago? For a retreat worthy of the First Couple, we recommend taking up at the Hyatt Regency Chicago. Back in 2008, the Obamas watched the results come in on election night from the hotel—but a weekend in the Monarch Suite would be all about the Four-Diamond-rated amenities, such as the Lakeshore Athletic Club and Stetson's Chop House.

If the Obamas are more of the toes-in-the-sand type, a weekend in the President's native Hawaii might be just the thing. The Royal Suite at the St. Regis Princeville on Kauai features private butler service, an intimate adjoining spa with a marble tub for two, and a furnished outdoor terrace with views of Hanalei Bay and Bali Hai mountain. If you actually leave the suite, the hotel also offers two golf courses, an infinity pool, and a restaurant by Jean-Georges.